Anthraquinone dyestuffs



PatentedtAug. 14,1945

'nryyco-pendin'g application-' S Patent5N 0.-:2,309,17-6") A" x Tlhe r present invention tainin'g an hydroxyalkyl '{group esterified with an organic 'carboxylioacid radicle-and includes the production ofthes 'n'ovel dyestuffs; for exa ple byfany one of the -followi-ng-' process'es:'

K0,) By t'esterifying an n'thraquinone' 'dyestufi' 1 group; attached to an aromatic nucleus either." directly or through If a' -1e atom-which isf'an oxygen; sulphur-or ni trogen atom, with an organic carboxylic acid esteriiyingj agent, ior' example an organic'carcontaining an hydroxyal boxylic-acid; acid anhydride or acid chloride.

(1)) By reacting an anthraquinone dyestuff containing a reactive hydrogen atom contained in an amino-group, an hydroxy grouper a mercaptan group with a reagent containing both a reactive halogen atom and an hydroxyalkyl group esterified with an organic carboxylic acid radicle. For example, an anthraquinone derivative containing a primary or secondary amino group may a be reacted with beta-chlorethyl'acetate.

(0) By reacting an anthraquinone dyestuff containing a carboxylic acid or'carboxylic acid halide group with a compound containing a hydroxy group and an' hydroxyalkyl groupesterified with an organic carboxylic acid radicle, e. -'g.,

glycol monoacetate. v

(d) By reacting an anthraquinone dyestufi containing a reactive hydrogen atom with a halo-' hydrin' .in the presence of a salt of an organic carboxylic acid.

- hydroxyalkyl groups, as, for example, in 1- acetoxyethylamino 4. -f amino anthraquinone (produced by reacting 1:4-diamino-anthraquinone with the calculated quantity of chlorethyl acetate in the presence of sodium acetate), or by alkylor aryl groups. If the esterified hydroxy- I.This:iinventionrelates to themanufacture of new anthraquinone dyestuffs and is a divisionof N0. 'zszyeemo comprises certain new dyestuffs, namely anthi' aquinone dyestuffs conthan one i .z'cs mi l .T RAQU N PE$ UFF HenryIEDreyfus;-:London, England, assignor'i'to' Gelaneseflorporation of America, .a corporation 1 1-:

o'lji'awing. ,origi alap lieauon October 19, 1937;" seriaino. 232;796. Divided and this ap""" li'cation May- 30, -1942, Serial.No.r,445,19'Z In GreatBr-itain: October 19, f

" ena e s; (o1. 260 .376i

alkyl. groupsfin dyestufis at. at ed "t the 1- and/or 4-positi0ns they are preferably active halog in the 2- and/or 3-positions I o eqlass of anthraquinone dyestuf fs included within masc ts of the presentinventionare;

those obtained'by introducing esterified hydroxy-3 alkyl groups 7 into ant taquindne con'taining cycloaliphatically 1substitute(:1 carboxylic amide groups and reactive'hydr genatoms tained iri ammo oup 'by-rea tmg the 7 qui'none fderiv'atives 'wi'th imltallzlin f p u ds. .e en w en no co n g es eriij hydrbxvalk l' s upaam dream are a caster andether materials. An example-bi suz co pounds is 1 :4-diamin0-anthraquinone-2-car:

' boxylic acid cyclohexylamide, obtained bytreating 1-amino-4-b-rom-anthraquinone-2-carboxylic ether and ester materials.

,est importance in the colouration of cellulose aceacid cyclohexylamide with excess of ammonia at C. It may beconverted into a dyestuff ace, cording to the present invention by reaction with chlorethyl acetate in the presence of sodium I acetate. 7

Whilst reference has been made above, only to acetic esters of the hydroxyalkyl compounds,

esters of other organic carboxylic acids may be tate materials, but as examples of other esters and ethers' of cellulose which may be coloured by means of them, reference may be made to cellulose formate, propionate and butyrate and to the ethyl, butyl and benzyl ethers of cellulose; The new dyestuffs may also be employed in the colouration of mixed materials comprising one or more of the, aforesaid cellulose esters or ethers in admixture With other textile fibres, for, example, wool, silk or other animal fibres, or cotton, regenerated cellulose or other cellulosic materials. Such other fibres may be coloured by the same dyestuffs as the cellulose esters or ethers'when they possess the requisite aflinity, or they may be coloured either in the same or diiierent shades by means of other dyestuffs either before, after or simultaneously with the colouration of the cellulose esters or ethers.

The new dyestuffs may be applied to textile materials in solution where they are sufficiently soluble, in aqueous suspension or after being brought into colloidal form, and it'is to be understood that the invention includes dyeingcompositions which contain the dyestuffs in conjunction with dispersing agents and/or protective colloids..

The new dyestufis may be applied to the materials from an aqueous bath or may be printed or stencilled on to the materials. V

The following examples illustrate the invention but are not to be regarded as limiting it in any way:

Example I An anthraquinone dyestuff containing an ace-' toxyethylamino grouping is obtained by refluxing I finely divided 1-hydroxyethylamino-4phenylam ino-anthraquinone with the calculated quantity of acetic anhydride in glacial acetic acid for about 1-2 hours. I Example II esses described, compositions of matter containing the dyestuffs, the colouration of materials with the dyestuffs and the coloured materials so obtained. As previously indicated, the dyestuffs are of particular importance in the colouration of cellulose ether and cellulose ester materials. Dyestuffs containing 'a free hydroxyalkyl group as well as anesterified hydroxyalkyl group are especially valuable in this connection and these dyestufis arethe subject of my co-pending application; S; No. 232,796.

Having described my invention what I desire to secure by Letters Patent is:

1. Anthraquinone' dyestuffs containing in the nucleus a hydroxy-alkyl amino group esterified with a low r alkyl mono-carboxylic acid, and another nuclear amino group. I

2. Anthraquinone dyestuffs containing in the nucleus a hydroxy-alkyl amino group esterified with a lower alkyl mono-carboxylic acid and also a cyclo-aliphatically substituted carboxylic acid amide group. g

3. Anthraquinone dyestuffs containing in the 1- position a hydroxy-alkyl amino group, esterified with a lower alkyl m-ono-carboxylic acid, and in the 4-position an amino group.

4. Anthraquinone dyestuffs containing in the 1.- position a hydroxy-alkyl amino group esterified with a lower alkyl mono-carboxylic'acid, and in the 4-position an aryl-amino group. 3

5. Anthraquinone dyestufis containing inv the 1- position an acetoxyethylamino group and in the.

" HENRY DR YFUS. 

